Method of improving the cosmetic properties of hair by using aldehyde solution

ABSTRACT

1. A process for improving the appearance, the feel, the combing and the physical and mechanical properties of human hair which comprises applying to the hair for a period of time between 15 to 60 minutes at a temperature between 15* and 60* C. an aqueous solution of 0.01 to 8 percent by weight of an aldehyde selected from the group consisting of glycolaldehyde, glyceric aldehyde, glutaric aldehyde, terephthalic aldehyde, orthophthalic aldehyde, starch dialdehyde, 2-hydroxymethyl-4-methoxy-3-oxa-pentanedial 4,6-diformyl-2,4,8-trihydroxymethyl-3,5,7-trioxanonanedial and 4,6,8,11-tetraformyl-2,4,13-trihydroxymethyl-3,5,7,10,12-penta oxa tetradecane dial.

United States Patent Kalopissis et a1.

[54] METHOD OF IMPROVING THE COSMETIC PROPERTIES OF HAIR BY USING ALDEHYDE SOLUTION [72] Inventors: Gregorire Kalopissis, Paris; Jean-Louis Abegg, Perreux, both of France [73] Assignee: LOreal, Paris, France [22] Filed: May 13, 1970 [21] Appl. No.: 37,431

Related [1.8. Application Data [63] Continuation of Ser. No. 565,393, July 15, 1966,

abandoned.

[30] Foreign Application Priority Data July 29, 1965 Luxembourg ..49208 [52] US. Cl ..424/70 [51] Int. Cl. ...A6lk 7/06 [58] Field of Search ..424/70 [56] References Cited UNITED STATES PATENTS 2,801,216 7/1957 Yoder et a1 ..210/64 [4 1 May 23, 1972 2,886,401 5/1959 2,941,859 6/1960 3,033,851 5/1962 Schaefer et a1. ..260/233.3 3,479,427 1 1/1969 Lieberman et al ..424/70 X FOREIGN PATENTS OR APPLICATIONS 768,892 2/1957 Great Britain ..260/599 Primary Examiner-Albert T. Meyers Assistant ExaminerDoris .I. F underburk AttorneyCushman, Darby & Cushman [5 7] ABSTRACT 3 Claims, No Drawings METHOD OF IMPROVING THE COSMETIC PROPERTIES OF HAIR BY USING ALDEHYDE SOLUTION This is a continuation of application Ser. No. 565,393, filed July 15, 1966, now abandoned.

It is known that certain treatments carried out on living hair, such as bleaching and permanent waving, may have the effect of altering certain of its properties, such as its feel, its appearance, the ease with which it may be combed, its manageability, the possibility of subsequently dyeing it under satisfactory conditions and even in certain cases, the mechanical strength of the fiber.

Attempts have already been made to develop treatments which improve the cosmetic properties of hair, but such treatments either give only poor results or they can be advantageously applied only in very special cases.

The present invention, which is the result of long, systematic research, concerns a treatment which may be applied in practically all cases and on practically all hair and which substantially improves the cosmetic properties thereof.

One object of the present invention is a new process for treating hair with a view to improving its cosmetic properties. This process is essentially characterized by the fact that an aqueous solution is applied to the hair, said solution containing at least one compound selected from the group consisting of aliphatic or aromatic dialdehydes, aldehyde alcohols, aldehyde polyalcohols and polyaldehyde polyalcohols.

According to the invention, the use of aqueous or water-alcohol compositions is preferred, these compositions containing about 0.01 to 8 percent of active compounds such as those mentioned above. These compositions are applied to the hair during a period of from 15 to 60 minutes, for example, at a temperature of from 15 to 60 C. and preferably around 35 to 40 C.

Among the active compounds which may be used according to the invention are glycolaldehyde, glyceric aldehyde, glutaric aldehyde, terephthalic aldehyde, orthophthalic aldehyde, starch dialdehyde, 2-hydroxymethyl-4-methoxy-3-oxa pentane dial, 4,6-diformyl-2,4,8-trihydroxymethyl-3,5,7-trioxanonanedial, 4,6,8,11-tetraformyl-2,4,13-trihydroxymethyl- 3,5,7,10,12-penta oxa tetradecane dial and, in general, dialdehydes obtained by oxidizing monoor polysaccharides with a periodic acid, these dialdehydes having given particularly valuable results in the tests which have been run.

The treatment process according to the invention has been shown to be practically universal and may be used in numerous cases such as: on natural hair, on hair more or less strongly bleached, on permanently waved hair and even in certain cases on hair in the reduced state, such as when the first stage of a conventional permanent wave has been carried out and when the treatment according to the invention is carried out before the second so-called neutralization stage.

An improvement in the cosmetic properties of the hair is noted in all cases utilizing an application according to the invention, the hair having a better appearance, a better feel, combing and untangling better, holding a set or a permanent better and showing good physical and mechanical properties.

Moreover, the applicants have noted with surprise that the treatment according to the invention permits a notable reduction in the alkaline solubility of the hair, as compared to the results obtained in the course of prior experiments carried out on wool, using solutions containing aldehydes.

It was heretofore believed that only unsaturated aldehydes would react with keratin and that saturated aldehydes having a longer chain than formic aldehyde had no effect on wool.

In any event, and however surprising the results concerning alkaline solubility may be, the treatment process according to the invention offers above all the possibility of improving the cosmetic properties of hair and also diminishing the alkaline solubility of the latter, which may be advantageous in certain cases.

Another object of the present invention is to provide the new article of manufacture consisting of a composition permitting the treatment of hair with a view to improving its cosmetic properties. This composition is essentially characterized by the fact that it contains at least one compound chosen from the group consisting of aliphatic or aromatic dialdehydes, aldehyde alcohols, aldehyde polyalcohols or polyaldehyde polyalcohols.

The compositions according to the invention may be in the form of aqueous or water-alcohol solutions of the active compounds named above, the concentration of the active compounds ranging for example from 0.01 to 8 percent, and the pH of these compositions varying from 3 to 10.

Another object of the present invention is to provide a composition for the treatment of hair, characterized by the fact that it contains at least one of the following compounds: glycolaldehyde, glyceric aldehyde, glutaric aldehyde, terephthalic aldehyde, orthophthalic aldehyde, starch dialdehyde, Z-hydroxy-methyl-4-methoxy-3-oxa pentane dial, 4,6- diformyl-2,4,8-trihydroxy-methyl-3,5,7-trioxa nonanedial, 4,6,8,11-tetraformyl-2,4,l3-trihydroxymethyl-3,5,7,10,12- penta oxa tetradecane dial, and, in general dialdehydes obtained by oxidizing monoor polysaccharides with periodic acid.

In order to make the invention more clearly understood, several embodiments thereof will be described in the following examples, solely by way of illustration and without limiting the scope of the invention to the details thereof.

EXAMPLE 1 After having rigorously bleached a womans hair, a lotion according to the invention is applied to half of it, this lotion consisting of a 1 percent aqueous solution of glutaric aldehyde. The application is made on dampened hair.

It is allowed to sit for 30 minutes at a temperature of 40 C. under a plastic hood. After this, the hair is suitably rinsed.

Next all of the hair is dyed using oxidation dyes.

It is noted that on the side of the coiffure which has been treated according to the invention the hair is clearly easier to comb, whether wet or dry. Moreover, that part of the hair is softer and less electric and the color is also more satisfactorily set therein.

EXAMPLE 2 Half of a coiffure which has been previously washed and dried is treated with a lotion according to the invention, this lotion consisting of a 4 percent solution of glutaric aldehyde.

It is allowed to sit for 30 minutes at a temperature of 40 C. under a plastic hood. Then the hair is rinsed and dried.

The whole head of hair is then rigorously bleached, followed by redyeing using oxidation dyes.

It is noted that on the side of the coiffure which has been treated according to the invention, the hair is much easier to comb, whether wet or dry. Moreover, on the treated side, the

hair is softer, silkier, less electric and has a healthier appearance.

EXAMPLE 3 Half of a dampened coiffure, which was previously rigorously bleached, is treated with a lotion according to the invention, this lotion consisting of a 1 percent aqueous solution of glycol-aldehyde.

After a 30-minute wait under a plastic hood at a temperature of 40 C., the hair is carefully rinsed.

Next the whole head of hair is dyed using oxidation dyes.

It is noted that on the treated side the hair is softer and healthier and easier to comb out.

After a period of two months, the hair is given a permanent without a new application of the lotion according to the invention.

It is noted that on the treated side, the hair is much softer and much easier to comb out whether wet or dry. Moreover, on the treated side, the hair curls more beautifully.

EXAMPLE 4 Half of a dampened coiffure is treated with a lotion according to the invention, this lotion consisting of a 50 percent water-alcohol solution containing 1 percent terephthalic aldehyde.

It is allowed to sit for thirty minutes at the ambient temperature under a plastic hood. Then the hair is carefully rinsed and dried.

Next the whole coiffure is rigorously bleached, then dyed in pastel shades.

it is noted that on the treated side the hair looks more healthy, shines more and is stronger.

EXAMPLE 5 EXAMPLE 6 A lotion according to the invention is applied to half of a dampened coiffure which has previously been rigorously bleached. This lotion consists of a 4% aqueous solution of starch dialdehyde.

After a 40 minute wait under a plastic hood, the hair is carefully rinsed.

it is noted that on the side treated according to the invention, the hair is easier to comb out whether wet or dry and is also softer, less electric, shinier and stronger.

EXAMPLE 7 A lotion according to the invention is applied to half of a coiffure which has previously been rigorously bleached. This lotion consists of an aqueous solution containing 0.02 percent glutaric aldehyde.

Next there is a 30 minute wait at a temperature of 45 C. under a plastic hood.

The hair is rinsed and redyed.

it is noted that on the side treated according to the invention, the hair is easier to comb out, softer and looks more healthy.

EXAMPLE 8 Half of a coiffure is treated with a lotion according to the invention, this lotion consisting of an aqueous solution containing 0.2 percent glutaric aldehyde, 0.2 percent starch dialdehyde, and 0.2 percent perfume.

There is a 10 minute wait under a plastic hood at the ambient temperature.

The hair is rinsed, dried and rigorously bleached.

It is noted that on the side treated according to the invention, the hair is shinier and more pliant.

EXAMPLE 9 Half of a coiffure is treated for 30 minutes at a temperature of 45 C. under a plastic hood with a lotion according to the invention, this lotion consisting of an aqueous solution containing 1 percent starch dialdehyde.

The hair is rinsed, then given a rigorous bleaching followed immediately by a soft permanent of the finest type.

It is noted that on the side treated according to the invention, the hair is shinier, the curl is more tractable and the ends are softer.

EXAMPLE 10 Half of a coiffure which has previously been rigorously bleached is treated with a lotion according to the invention, this lotion consisting of an aqueous solution containing 0.3 percent ethyl-cellulose, 0.5 percent phenylethyl alcohol, 0.5 percent glutaric aldehyde and 0.1 percent perfume.

There is a 30 minute wait under a plastic hood at the ambient temperature.

It is noted that on the side treated according to the invention, the damp hair is softer and silkier.

When dry, the hair is also shinier, the ends are softer and it is easier to comb out.

EXAMPLE 11 A 2 percent aqueous solution of 2-hydroxymethyl-4- methoxy-3-oza-pentane dial is applied to bleached hair for thirty minutes at a temperature of 45 C. under a plastic hood.

After this treatment, the hair is softer, shinier and easier to comb out.

EXAMPLE 12 A mixture of '90 grams of an aqueous solution containing 0.2 percent glutaric aldehyde, 0.2 percent starch dialdehyde and 1 percent Cemulsol 132 is placed in an aerosol bomb with ten grams of Freon 12.

The foam thus obtained is applied to the dampened hair after shampooing.

The combing out is much improved. The hair is softer and the ends silky. The curl is tractable.

Cemulsol 132 is a polyethoxylated ether of a polyarylphenol having a density at 20 C. of 1145-1150, a viscosity at 20 C. of 500 i 50 centipoises, a solidification point of +7 C. and an acid index of 1, max.

Freon 12 is dichlorodifluoromethane.

EXAMPLE 13 To one side of a previously totally bleached coiffure is applied an aqueous solution containing 2 percent by weight of 4,6-diformyl-2,4,8-trihydroxymethyl-3,5,7-trioxa nonane dial obtained by periodic oxidation of saccharose, and 1 percent perfume.

This is heated by conventional means under a hood to a temperature of about 50 C. for 30 minutes.

After having finished the treatment, it is noted that on the treated side the hair is shinier, healthier and feels better to the touch.

EXAMPLE 14 A coiffure is entirely bleached, then redyed using the finest quality oxidation dyes. Then one side of the coiffure is treated with a solution containing 4 percent 4,6,8,1l-tetraformyl- 2,4,l3-trihydroxymethyl-3,S,7,10,12-penta oxa tetradecane dial obtained by oxidizing raffinose.

Without being rinsed, the hair is then set using conventional heating means, for example, under a hood, at a temperature of 45 C. for 30 minutes.

After having finished the treatment, it is noted that on the treated side, the hair is healthier, shinier and feels better to the touch. The ends are also less rough.

We claim:

1. A process for improving the appearance, the feel, the combing and the physical and mechanical properties of human hair which comprises applying to the hair for a period of time between 15 to 60 minutes at a temperature between 15 and 60 C. an aqueous solution of 0.01 to 8 percent by weight of an aldehyde selected from the group consisting of glycolaldehyde, glyceric aldehyde, glutaric aldehyde, terephthalic aldehyde, orthophthalic aldehyde, starch dialdehyde, 2-hydroxymethyl-4-methoxy-3-oxa-pentanedial, 4,6- diformyl-2,4,8-trihydroxymethyl-3,5,7-trioxanonanedial and 4,6,8,l1-tetraformyl-2,4, 13-trihydroxymethyl-3,5,7,10,12- penta oxa tetradecane dial.

2. The process of claim 1 wherein said aldehyde is present in amounts ranging between 4 to 6 percent by weight of said solution.

3. The process of claim 1 wherein the temperature ranges between and 45 C. 5 

1. A PROCESS FOR IMPROVING THE APPEARANCE, THE FEE, THE COMBING AND THE PHYSICAL AND MECHANICAL PROPERTIES OF HUMAN HAIR WHICH COMPRISES APPLYING TO THE HAIR FOR A PERIOD OF TIME BETWEEN 15 TO 60 MINUTES AT A TEMPERATURE BETWEEN 15* AND 60*C. AN AQUEOUS SOLUTION OF 0.01 TO 8 PERCENT BY WEIGHT OF AN ALDEHYDE SELECTED FROM THE GROUP CONSISTING OF GLYCOLALDEHYDE, GLYCERIC ADEHYDE, GLUTARIC ADEHYDE, TEREPHTHALIC ALDEHYDE, ORTHOPHTHALIC ADEHYDE, STARCH DIALDEHYDE, 2-HYDROXYMETHYL-4-METHOXY-3-OXA-PENTANEDIAL 4,6DIFORMLY-2,4,8-TRIHYDROXYMETHYL-3,5,7-TRIOXANONANEDIAL AND 4,6,8,11-TETRAFORMYL-2,4,13-TRIHYDROXYMETHYL-3,5,7,10,12PENTA OXA TETRADECANE DIAL.
 2. The process of claim 1 wherein said aldehyde is present in amounts ranging between 4 to 6 percent by weight of said solution.
 3. The process of claim 1 wherein the temperature ranges between 30* and 45* C. 